開發可3D列印暨抗菌材料應用於傷口敷料研究

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研究生：	王嘉淳 Wang, Chia-Chun
論文名稱：	開發可3D列印暨抗菌材料應用於傷口敷料研究 The Development of 3D-Printable and Antimicrobial Materials for Wound Dressing
指導教授：	王潔 Wang, Jane
口試委員:	朱一民 Chu, I-Min 衛子健 Wei, Tzu-Chien 姚少凌 Yao, Chao-Ling 費安東 Venault, Antoine
學位類別：	博士 Doctor
系所名稱：	工學院 - 化學工程學系 Department of Chemical Engineering
論文出版年：	2021
畢業學年度：	109
語文別：	英文
論文頁數：	149
中文關鍵詞：	傷口敷料、抗菌功能、3D列印
外文關鍵詞：	Wound dressing, Antimicrobial function, 3D-printing
相關次數：	點閱：3 下載：0
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為了促進傷口癒合並提高治療品質，本論文旨在開發新型的材料，該材料能夠順應傷口的形狀並具有抗菌性能，以提高患者的接受度並預防傷口感染。基於這些需求，本研究提出新的策略並開發具有3D列印和抗菌功能的材料。
首先，將精氨酸以化學鍵結修飾於聚（癸二酸甘油酯）高分子鏈上，開發PGS-g-Arg接枝材料，其機械性能，水蒸氣透過率，抗菌功能和生物相容性均經由實驗得到了證實。材料的楊氏模數可透過不同精氨酸接枝率進行調控，另外，發現在7 ~ 13% 的精氨酸接枝率，PGS-g-Arg材料的拉伸強度與皮膚相似。這些材料的水蒸氣透過率範圍為6.1至10.3 g / m2 / h，顯示具有形成水氣屏障的功能並有助於傷口癒合。在精氨酸接枝率為7 % 的PGS-g-Arg材料上即具有95 % 以上的抗菌功能，並透過體外相容性實驗也確認這些開發材料具有生物相容性。
其次，利用數位光處理積層製造技術 (DLP-AM) 的快速原型製造且高解析度的優勢來製備傷口敷料以順應傷口形狀。然而，光起使劑是此製造技術中的重要成分，若產生細胞毒性將限制了DLP-AM在傷口敷料中的應用。因此，針對應用於DLP-AM的光起始劑進行了深入研究。將4種常見的光起使劑與光固化材料結合，並通過探索聚合條件，機械性能和生物相容性來分析其特性。最終篩選出維生素B2和三乙醇胺（B2 / TEOA）的組合適用於DLP-AM。
最後，將可光交聯的PGS-g-Arg 材料與B2 / TEOA結合使用，並通過DLP-AM 製造3D列印抗菌傷口敷料。結果證實 “60 wt% PGSA” 與 “40 wt% PGS-g-18％Arg” 和 “ 0.5 wt% B2 / TEOA光起始劑” 的組合可通過DLP-AM進行3D列印。此新組合材料可快速列印受傷的組織，同時具抗菌功能與安全性將可望應用於傷口敷料。

In order to promote wound healing and improve the quality of treatment, this thesis aims to develop novel materials that can conform to the shape of wounds and have antimicrobial properties to increase patient tolerance and prevent wound infections. Based on these requirements, novel strategies were conducted and materials with 3D printing and antimicrobial functions were developed.
First, L-arginine grafted poly(glycerol sebacate) materials (PGS-g-Arg) were developed by chemical conjugation of L-arginine on poly(glycerol sebacate) chains. The characteristics of mechanical property, water vapor transmission rate, antimicrobial functions, and biocompatibility of grafted materials were investigated. At various L-arginine grafting ratio, the mechanical properties are tunable. It was found that between 7–13% L-arginine grafting ratios, the tensile strengths of PGS-g-Arg were similar to that of natural skin. These materials were shown with a low water vapor transmission rate, 6.1 to 10.3 g/m2/h, which would form a barrier and assist in the closure of wounds. The grafting ratio of 7% L-arginine on PGS polymers are more than 95% efficient in antimicrobial functions, and a series of experiments were conducted to confirm its biocompatibility.
Second, utilizing the advantage of rapid prototyping with high efficiency and high resolution, digital light processing additive manufacturing (DLP-AM) is one of the suitable methods to fabricate wound dressings that conform to the shape of wounds. However, some photoinitiators, as one of the key components in DLP-AM, may present toxicity and greatly limit the application of DLP-AM toward wound dressing. Therefore, a thorough study on the selection of photoinitiators used in DLP-AM was conducted. Four common photoinitiators were combined with photocurable materials and their characteristics were analyzed by exploring the polymerization conditions, mechanical properties, and biocompatibility. The combination of vitamin B2 and triethanolamine (B2/TEOA) shows more potential to apply in DLP-AM.
Finally, photocrosslinkable PGS-g-Arg materials are combined with B2/TEOA for the 3D printing of antimicrobial wound dressings through DLP-AM. It is proven that the combination of "60 wt% of PGSA" mixed with "40 wt% of PGS-g-18%Arg" and "0.5 wt% of B2/TEOA photoinitiator” are 3D-printable through DLP-AM. This novel combination enables the rapid printing of wounded tissue, and is highly applicable as a nontoxic and antimicrobial wound dressing.

摘要    I
Abstract    II
謝誌    IV
Table of Content    V
List of Figures    XIII
List of Tables    XVIII
Chapter 1. Preface    1
Chapter 2. Research Background    4
2-1 Wound Dressing    4
2-1-1 Traditional Wound Dressings    5
2-1-2 Modern Wound Dressings    5
2-1-2-1 Semi-permeable Film Dressing    5
2-1-2-2 Semi-permeable Foam Dressing    6
2-1-2-3 Hydrogel Dressing    6
2-1-2-4 Hydrocolloid Dressing    6
2-1-2-5 Bioactive Wound Dressing    7
2-1-2-6 Silicone Patch Dressing    7
2-1-2-7 Composite Dressing    7
2-2 The Introduction of Additive Manufacturing    9
2-2-1 Fused Deposition Modeling (FDM)    9
2-2-2 Stereolithography (SLA)    10
2-2-3 Selective Laser Sintering (SLS)    11
2-2-4 Digital Light Processing Additive Manufacturing (DLP-AM)    11
2-3 Introduction of Materials with Antimicrobial Activity and Their Mechanism Research    12
2-3-1 Antibiotics    13
2-3-2 Silver Nanoparticles    15
2-3-3 Cationic Amino Acids    18
Chapter 3. Development of Poly (Glycerol Sebacate)-Grafted-Cationic Amino Acid Polymers with Antimicrobial Activity    21
3-1 The Introduction of Poly (Glycerol Sebacate)    21
3-2 Research Framework    25
3-3 Materials and Methods    27
3-3-1 Materials and Instruments    27
3-3-2 Fabrication of Cationic Amino Acids Grafted Poly (Glycerol Sebacate) Prepolymers    29
3-3-2-1 Synthesis and Purification of PGS-g-Cationic Amino Acid Prepolymers    29
3-3-2-2 Structural Analyses of PGS-g-Cationic Amino Acid Prepolymers    31
3-3-3 Fabrication of Cationic Amino Acids Grafted Poly (Glycerol Sebacate) Crosslinking Films    31
3-3-3-1 Synthesis of PGS-g-Cationic Amino Acid Crosslinking Films    31
3-3-3-2 Structural Analyses of PGS-g-Cationic Amino Acid Crosslinking Films    32
3-3-4 Characteristics of Cationic Amino Acid Grafted Poly (Glycerol Sebacate) Crosslinked Films    32
3-3-4-1 Mechanical Property Test    32
3-3-4-2 Swelling Ratio Test    32
3-3-4-3 Water Vapor Transmission Rate Test (WVTR)    33
3-3-4-3-1 Vial Method    33
3-3-4-3-2 Mocon Method    34
3-3-4-4 Antimicrobial Test    34
3-3-4-5 Cytocompatibility of Cationic Amino Acid Grafted Poly (Glycerol Sebacate) Crosslinked Films    35
3-3-4-5-1 Cell Culture    35
3-3-4-5-2 Agar Diffusion Test    35
3-4 Results and Discussion    37
3-4-1 Fabrication of Cationic Amino Acid grafted Poly (Glycerol Sebacate) Prepolymers    37
3-4-1-1 Synthetic Methods of PGS-g-Cationic Amino Acids    37
3-4-1-2 Purification Method of PGS-g-Cationic Amino Acids    39
3-4-1-3 1H-NMR Analyses of Poly (Glycerol Sebacate) and L-arginine Grafted Poly (Glycerol Sebacate) Prepolymers    41
3-4-2 Fabrication of Cationic Amino Acid grafted Poly (Glycerol Sebacate) Crosslinking Films    44
3-4-2-1 Fabrication of Crosslinking Films via Polycondensation    44
3-4-2-2 FT-IR Analyses of Crosslinking Films    45
3-4-3 Mechanical Property and Swelling Ratio of Crosslinking Films    46
3-4-4 Water Vapor Transmission Rate of Crosslinking Films    48
3-4-5 Antimicrobial Function of Crosslinking Films    51
3-4-6 Cytocompatibility Evaluation of Crosslinking Films    53
3-5 Summary    55
Chapter 4. The Study of Highly Biocompatible Photoinitiators for the Photocurable Polymers and Their Applications of Digital Light Processing Additive Manufacturing    56
4-1 Introduction    56
4-1-1 The Introduction of Photopolymerization Reaction    56
4-1-2 Biocompatible and Photocurable Polymers    57
4-1-2-1 Poly (ε-Caprolactone) Diacrylate Derivatives    61
4-1-2-2 Poly (Glycerol Sebacate) Acrylate    62
4-1-3 Photoinitiators    64
4-1-3-1 2, 2-Dimethoxy-2-Phenylacetophenone (DMPA)    65
4-1-3-2 Diphenyl (2, 4, 6-Trimethylbenzoyl) Phosphine Oxide (TPO)    65
4-1-3-3 2-Hydroxy-4’-(2-Hydroxyethoxy)-2-Methylpropiophenone (I2959)    66
4-1-3-4 Riboflavin (Vitamin B2) Combined with Triethanolamine (TEOA)    66
4-1-4 Photoinitiator Cytocompatibility    69
4-2 Research Framework    72
4-3 Materials and Methods    74
4-3-1 Materials and Instruments    74
4-3-2 Absorbance Spectra Analyses of Photoinitiators    76
4-3-3 Fabrication of Photocrosslinkable Prepolymers    76
4-3-3-1 Synthesis of Poly (Glycerol Sebacate) Acrylate Prepolymers (PGSA)    76
4-3-3-2 Synthesis of Poly (ε-Caprolactone) Diacrylate Prepolymers (PCLDA)    77
4-3-4 Structural Analyses of Photocurable Prepolymers    78
4-3-5 Fabrication of PGSA and PCLDA Films    78
4-3-5-1 Miscibility Test between Photoinitiators and Photocurable Prepolymers    78
4-3-5-2 UV-curing Analyses of Photoinitiators and Photocurable Prepolymers    79
4-3-6 Mechanical Property Test of Films    79
4-3-7 In vitro Biocompatibility Study    80
4-3-7-1 Cell Culture    80
4-3-7-2 Cytocompatibility Comparison of Photoinitiators    80
4-3-7-3 Cytocompatibility Test of Films    82
4-3-7-4 Cell Proliferation Test of Films    82
4-3-8 In vivo Biocompatibility Study    83
4-3-8-1 Histological Analyses of Harvested Tissues    84
4-3-8-2 Immunoassay Analyses of Harvested Tissues    84
4-3-9 Fabrication of Designed Patterns via Digital Light Processing Additive Manufacturing System (DLP-AM)    84
4-3-9-1 Printing Applicability through DLP-AM System    84
4-3-9-2 Mechanical Property Test of DLP-AM Printed Patterns    85
4-4 Results and Discussions    86
4-4-1 UV-Vis Absorbance Spectra of Photoinitiators    86
4-4-2 1H-NMR Analyses of Photocurable Prepolymers    88
4-4-3 Photopolymerization Analyses between Photoinitiators and Photocurable Prepolymers    90
4-4-3-1 Miscibility Analyses and PGSA Films Fabrication    90
4-4-3-2 Miscibility Analyses and PCLDA Films Fabrication    93
4-4-4 Mechanical Property of Films    97
4-4-5 Cytocompatibility of Photoinitiators    100
4-4-6 Cytocompatibility of Films    102
4-4-6-1 Cytocompatibility of PGSA Films    102
4-4-6-2 Cytocompatibility of PCLDA Films    104
4-4-7 Cell Proliferation of PGSA Films    105
4-4-8 In vivo Biocompatibility of PGSA Films    107
4-4-9 Application in DLP-AM Printing Method    111
4-5    Summary    114
Chapter 5. Development of Poly (Glycerol Sebacate)-grafted-(Arginine-co-Acrylate)    115
5-1 Research Framework    115
5-2 Materials and Methods    117
5-2-1 Materials and Instrument    117
5-2-2 Fabrication of Poly (Glycerol Sebacate)-grafted-(Arginine-co-Acrylate)    118
5-2-2-1 Synthesis of Poly (Glycerol Sebacate) Acrylate prepolymers modified with L-Arginine    118
5-2-2-2 Synthesis of Poly (Glycerol Sebacate)-grafted-Arginine modified with Acryloyl Chloride    119
5-2-2-3 Structural Analysis of Poly (Glycerol Sebacate)-grafted-(Arginine-co-Acrylate)    120
5-2-3 Blending of PGS-g-Arg prepolymers and PGSA prepolymers    120
5-2-4 UV-crosslinking Feasibility of Photoinitiators and Photocurable Prepolymers    120
5-2-5 Structural Analysis of Crosslinked Films    121
5-2-6 Printing Applicability through DLP-AM System    121
5-3 Results and Discussion    122
5-3-1 Fabrication and 1H-NMR Analyses of Poly (Glycerol Sebacate)-grafted-(Arginine-co-Acrylate)    122
5-3-2 UV-crosslinking Capability Analyses    124
5-3-2-1 UV-crosslinking Capability Analyses of PGS-g-(Arg-co-Acrylate) Prepolymers and Photoinitiators    124
5-3-2-2 UV-crosslinking Capability Analyses of Blended Polymers of PGS-g-Arg and PGSA Prepolymers and Photoinitiators    126
5-3-3 FT-IR Analysis of Crosslinked Films    128
5-3-4 DLP-AM Printing Feasibility Analysis of Blended Polymers    129
Chapter 6. Conclusion and Future Prospects    130
References    131
Appendix A. The Calculated Expression of Quantified Data of Morphological Grades    141
Appendix B. Published paper in Polymers 2020, 12, 1457    142
Appendix C. Histological Images of Harvested Tissue in the groups of PGS Films    143
Appendix D. Histological Images of Harvested Tissue in the groups of PGSA-0.5%B2/TEOA Films    147

                                

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